WO2008044695A1 - Dispositif de transistor organique à couche mince et transistor organique à couche mince émetteur de lumière - Google Patents

Dispositif de transistor organique à couche mince et transistor organique à couche mince émetteur de lumière Download PDF

Info

Publication number
WO2008044695A1
WO2008044695A1 PCT/JP2007/069729 JP2007069729W WO2008044695A1 WO 2008044695 A1 WO2008044695 A1 WO 2008044695A1 JP 2007069729 W JP2007069729 W JP 2007069729W WO 2008044695 A1 WO2008044695 A1 WO 2008044695A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
thin film
organic thin
film transistor
Prior art date
Application number
PCT/JP2007/069729
Other languages
English (en)
Japanese (ja)
Inventor
Yuki Nakano
Masatoshi Saito
Hiroaki Nakamura
Original Assignee
Idemitsu Kosan Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Idemitsu Kosan Co., Ltd. filed Critical Idemitsu Kosan Co., Ltd.
Priority to JP2008538733A priority Critical patent/JP5368797B2/ja
Priority to EP07829467A priority patent/EP2073290A4/fr
Priority to US12/445,146 priority patent/US8217389B2/en
Priority to CN200780037982XA priority patent/CN101523631B/zh
Publication of WO2008044695A1 publication Critical patent/WO2008044695A1/fr

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/221—Carbon nanotubes
    • H10K85/225—Carbon nanotubes comprising substituents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C09B3/78—Other dyes in which the anthracene nucleus is condensed with one or more carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/30—Organic light-emitting transistors
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/60—Forming conductive regions or layers, e.g. electrodes
    • H10K71/611—Forming conductive regions or layers, e.g. electrodes using printing deposition, e.g. ink jet printing
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/464—Lateral top-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
    • H10K10/80—Constructional details
    • H10K10/82—Electrodes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details

Definitions

  • the present invention relates to an organic thin film transistor and an organic thin film light emitting transistor, and more particularly to an organic thin film transistor including a compound having a high mobility and capable of high speed operation, and an organic thin film light emitting transistor using the same. .
  • a thin film transistor is widely used as a switching element for display in a liquid crystal display device or the like.
  • Figure 3 shows a typical TFT cross-sectional structure.
  • a TFT has a gate electrode, an insulator layer, and an organic semiconductor layer in this order on a substrate, and has a source electrode and a drain electrode formed on the organic semiconductor layer at a predetermined interval.
  • the organic semiconductor layer forms a channel region, and is turned on / off by controlling the current flowing between the source electrode and the drain electrode with the voltage applied to the gate electrode.
  • this TFT has been manufactured using amorphous or polycrystalline silicon. CVD devices used to manufacture TFTs using such silicon are very expensive and display devices using TFTs.
  • TFTs using organic substances instead of amorphous or polycrystalline silicon have been proposed! /.
  • Vacuum deposition and coating methods are known as film formation methods used when forming TFTs with organic materials.
  • these film formation methods can increase the size of the device while suppressing an increase in manufacturing costs. Therefore, the process temperature required for film formation can be made relatively low.
  • TFTs using organic substances have the following advantages: there are few restrictions when selecting materials for the substrate, and they are expected to be put to practical use. TFT has been actively reported, for example, non-patent literature;! -20.
  • organic substances used in the organic compound layer of TFT include multimers such as conjugated polymers such as thiophenone (patent document;!
  • Patent Documents 7 and 8, etc. are used in the form of simple substances or mixtures with other compounds.
  • n-type FET materials for example,
  • TNNQD 11,11,12,12-tetracyanonaphtho-2,6-quinodimethane
  • NCDI 1,4,5,8_naphthalenetetracarboxyldiimide
  • 10 discloses a fluorinated phthalocyanine! /.
  • Patent Document 11 includes an organic semiconductor material having at least one structure in which a group containing an aromatic hydrocarbon ring or an aromatic heterocyclic ring is bonded via an alkynylene group and having a molecular weight of 2,000 or less.
  • Patent Document 12 describes the invention of a chenothiophene derivative, discloses a compound in which this chenothiophene derivative is bonded to benzene via acetylene, and describes its use for a thin-film transistor! / Such an example is described! /, Na! / ⁇
  • an organic electoric luminescence (EL) element as a device that uses electric conduction in the same way.
  • An organic EL element is generally forced by applying a strong electric field of 10 5 V / cm or more in the film thickness direction of an ultrathin film of lOOnm or less
  • a strong electric field of 10 5 V / cm or more in the film thickness direction of an ultrathin film of lOOnm or less
  • the above-mentioned compound in the conventional organic TFT has a problem in high-speed response as a transistor with low field-effect mobility and low response speed. Also, the on / off ratio was small.
  • the on / off ratio mentioned here is the value obtained by dividing the current flowing between the source and drain when the gate voltage is applied (on) by the current flowing between the source and drain when the gate voltage is not applied (off).
  • On-state current is the current value (saturation current) when the current flowing between the source and drain is saturated, usually by increasing the gate voltage.
  • Patent Document 2 JP-A-8-228035
  • Patent Document 3 Japanese Patent Laid-Open No. 9-232589
  • Patent Document 4 Japanese Patent Laid-Open No. 10-125924
  • Patent Document 5 Japanese Patent Laid-Open No. 10-190001
  • Patent Document 6 JP 2000-174277 A
  • Patent Document 7 Japanese Patent Laid-Open No. 5-55568
  • Patent Document 8 Japanese Patent Laid-Open No. 2001-94107
  • Patent Document 9 Japanese Patent Laid-Open No. 10-135481
  • Patent Document 10 Japanese Patent Application Laid-Open No. 11-251601
  • Patent Document 11 Japanese Patent Application Laid-Open No. 2004-179249
  • Patent Document 12 Japanese Patent Laid-Open No. 2003-73382
  • Non-patent document 1 F. Ebisawa et al., Journal of Applied Physics, 54, 3255, 1983
  • Non-patent document 2 A. Assadi et al., Applied Physics Letter, 53, 195, 1988
  • Non-patent document 3 G. Guillaud et al., Chemical Physics Letter, 167, 503, 1990
  • Non-patent document 4 X. Peng et al., Applied Physics Letter, 57, 2013, 1990
  • Non-patent document 5 G. Horowitz et al., Synthetic Metals, 41-43, 1127, 1991
  • Non-Patent Document 6 S. Miyauchi et al., Synthetic Metals, 41-43 ⁇ , 1991
  • Non-patent literature 7 H. Fuchigami et al., Applied Physics Letter, 63, 1372, 1993
  • Non-patent literature 8 H. Koezuka et al., Applied Physics Letter, 62, 1794, 1993
  • Non-patent literature 9 F Gamier et al., Science, 265, 1684, 1994
  • Non-patent literature 10 AR Brown et al., Synthetic Metals, 68, 65, 1994
  • Non-patent literature 11 A. Dodabalapur et al., Science, 268 ⁇ , 270, 1995
  • Non-patent literature 12 T. Sumimoto et al., Synthetic Metals, 86, 2259, 1997
  • Non-Patent Document 13 K. Kudo et al., Thin Solid Films, 331 ⁇ , 51, 1998
  • Non-patent document 14 K. Kudo et al., Synthetic Metals, 102, 900 pages, 1999
  • Non-patent document 15 K. Kudo et al., Synthetic Metals, 111-112, 11 pages, 2000
  • Non-patent document 16 Advanced Materials Volume 13, No. 16, 2001, p. 1273
  • Non-Patent Document 17 Advanced Materials Vol.15, No.6, 2003, p.478
  • Non-Patent Document 18 W. Geens et al., Synthetic Metals, 122, 191 pages, 2001
  • Non-Patent Document 19 Lay-Lay Chua et al., Nature, 434, March 10, 2005, p. 194
  • Non-Patent Document 20 C.D. Dimitrakopoulos et al., IBM J. RES. & DEV. Vol. 45, No. 11, p. 11, 2001
  • the present invention has been made to solve the above-mentioned problems, and has a high response speed (driving speed), a large force, and a large on / off ratio! /, And an organic thin film transistor using the same
  • An object is to provide an organic thin film light emitting transistor.
  • the response speed drive speed
  • the organic semiconductor layer of the organic thin film transistor has an aromatic hydrocarbon group at the center represented by the following general formula (1).
  • the inventors have found that the above object can be achieved by using a compound having an aromatic heterocyclic group and a structure having improved planarity as a compound, and the present invention has been completed.
  • a gate electrode, a source electrode, and a drain electrode, an insulator layer, and an organic semiconductor layer are provided on a substrate, and a source-drain current is controlled by applying a voltage to the gate electrode.
  • an organic thin film transistor in which the organic semiconductor layer contains a compound represented by the following general formula (1) is provided.
  • R to R each independently represent a hydrogen atom, a halogen atom
  • R to R and R to R are adjacent to each other to form a saturated or unsaturated cyclic structure.
  • Ar is an aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent and an aromatic heterocyclic group having 1 to 60 carbon atoms which may have a substituent.
  • n is an integer from ! ]
  • the present invention also provides an organic thin film light emitting transistor in which light emission is obtained by utilizing a current flowing between a source and a drain in an organic thin film transistor, and the light emission is controlled by applying a voltage to a gate electrode. is there.
  • the organic thin film transistor of the present invention has an improved response speed (driving speed), and has a high performance as a transistor having a large on / off ratio, and is an organic thin film light emitting transistor capable of emitting light. Can also be used.
  • FIG. 1 is a diagram showing an example of an element configuration of an organic thin film transistor of the present invention.
  • FIG. 2 is a diagram showing an example of the element configuration of the organic thin film transistor of the present invention.
  • FIG. 3 is a diagram showing an example of the element structure of the organic thin film transistor of the present invention.
  • FIG. 4 is a diagram showing an example of the element structure of the organic thin film transistor of the present invention.
  • FIG. 5 is a diagram showing an example of the element structure of the organic thin film transistor of the present invention.
  • FIG. 6 is a diagram showing an example of the element structure of the organic thin film transistor of the present invention.
  • FIG. 7 is a diagram showing an example of an element configuration of an organic thin film transistor in an example of the present invention.
  • FIG. 8 is a diagram showing an example of an element configuration of an organic thin film transistor in an example of the present invention.
  • FIG. 9 is a diagram showing an example of an element configuration of an organic thin film light emitting transistor in an example of the present invention.
  • FIG. 10 is a graph showing an emission spectrum of an organic thin film light emitting transistor in an example of the present invention.
  • the organic thin film light-emitting transistor of the present invention is provided with at least three terminals of a gate electrode, a source electrode, and a drain electrode, an insulator layer, and an organic semiconductor layer on a substrate, and a voltage between the source and drain is applied to the gate electrode.
  • the organic semiconductor layer contains a compound represented by the following general formula (1).
  • Ar is represented by the following general formula (2), and Ar is represented by the following general formula (3).
  • R to R each independently represent a hydrogen atom, a halogen atom,
  • an alkoxy group having 30 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, C1-C30 haloalkylthio group, C1-C30 alkylamino group, C2-C30 dialkylamino group (the alkyl groups may be bonded to each other to form a ring structure containing a nitrogen atom)
  • haloalkylsulfonyl group 6 to 60 aromatic hydrocarbon group, carbon number;!
  • substituent It may be an alkylsilyl group having 3 to 30 carbon atoms or a cyan group, and each of these groups may have a substituent.
  • R to R and R to R are adjacent to each other to form a saturated or unsaturated cyclic structure.
  • halogen atom examples include fluorine, chlorine, bromine and iodine atoms.
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexynole group, n-heptyl group, n-octyl group. Groups and the like.
  • haloalkyl group examples include, for example, a chloromethyl group, a 1-chloroethyl group, a 2-chloroethyl group, a 2-chloroethyl isobutyl group, a 1,2 dichloroethyl group, a 1,3 dichroic isopropyl group, 2, 3 Dichloro-t-butyl group, 1, 2, 3 Trichloropropyl group, bromomethyl group, 1 bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2 , 3-Jib mouth tert-butyl group, 1, 2, 3 Tribromopropyl group, odomethyl group, 1- odoethyl group, 2 podethyl group, 2 podisobutyl group, 1, 2 jordoethyl group, 1,
  • the alkoxyl group is a group represented by OX 1
  • examples of X 1 include the same examples as described for the alkyl group
  • the haloalkoxyl group is a group represented by OX 2
  • Examples of X 2 include the same examples as described for the haloalkyl group.
  • the alkylthio group is a group represented by SX 1 , and examples of X 1 include the same examples as described for the alkyl group, and the haloalkylthio group is represented by sx 2 Examples of X 2 include the same examples as described for the haloalkyl group.
  • the alkylamino group is a group represented by —NHX 1
  • the dialkylamino group is a group represented by NX
  • X 1 and X 3 are examples similar to those described for the alkyl group, respectively. Is mentioned.
  • Examples of the ring structure in which the alkyl group of the dialkylamino group may be bonded to each other to form a ring structure containing a nitrogen atom include pyrrolidine, piperidine and the like.
  • the alkylsulfonyl group is a group represented by SO X 1 , and examples of X 1 include the same examples as those described above for the alkyl group, and the haloalkylsulfonyl group is —SO X 2 Examples of X 2 include the same examples as described for the haloalkyl group.
  • aromatic hydrocarbon group examples include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a perylenyl group, a tetracenyl group, and a pentacenyl group.
  • Examples of the aromatic heterocyclic group include a dithienophenyl group, a benzofuranyl group, a benzothiophenyl group, a quinolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzothiadiazonyl group, and the like.
  • Examples of the alkylsilyl group, a group represented by -si ⁇ x 4, X 1, X 3 and X 4 include the same examples as those described for each of said alkyl groups.
  • saturated cyclic structure examples include a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • Examples of the unsaturated cyclic structure include the same examples as those described for the aromatic hydrocarbon group.
  • Ar represents an aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, and an aromatic hydrocarbon having 1 to 60 carbon atoms which may have a substituent. It is a heterocyclic group.
  • aromatic hydrocarbon group having 6 to 60 carbon atoms examples include divalent residues such as benzene, naphthalene, anthracene, phenanthrene, tetracene, taricene, and pentacene, and include benzene, naphthalene, anthracene, phenanthrene, Bivalent residues of tetracene and pentacene are preferred.
  • the aromatic heterocyclic group having 1 to 60 carbon atoms is preferably a condensed polycyclic aromatic heterocyclic ring having 6 to 60 carbon atoms (preferably 8 to 60 carbon atoms) (condensed polycyclic aromatic heterocyclic group).
  • a condensed polycyclic aromatic heterocyclic ring having 6 to 60 carbon atoms (preferably 8 to 60 carbon atoms) (condensed polycyclic aromatic heterocyclic group).
  • the divalent residues of dithienobenzene, benzothiophene, dibenzothiophene, benzofuran and dibenzofuran are preferred.
  • n is an integer of 1 to 20, and may be 1 or a plurality of 2 or more.
  • Force S preferably an integer of! When n is within the range of! ⁇ 20, it effectively coordinates with the substrate, contributing to the improvement of mobility.
  • R, R, R, R, R, R and R are all hydrogen atoms.
  • R and R is a halogen atom, an alkyl group having 1 to 8 carbon atoms, carbon
  • the compound preferably has a finer alignment structure.
  • the compound represented by the general formula (1) is preferably a compound represented by the following general formula (4).
  • R to R are the same groups as R to R in the general formula (1), respectively.
  • R to R, R to R, R to R are adjacent to each other
  • N is an integer of 1 to 20; preferably an integer of! To 5; When n is in the range of 1 to 20, it effectively coordinates with the substrate, which contributes to improvement of mobility.
  • R to R forces are each independently a hydrogen atom or a halogen atom.
  • a dialkylamino group having 2 to 8 carbon atoms (the alkyl groups may be bonded to each other to form a ring structure containing a nitrogen atom), an alkylsulfonyl group having 1 to 8 carbon atoms, or a cyan group is preferable. .
  • R, R, R, R, R, and R to R are all hydrogen atoms.
  • At least one of R and R is a halogen atom, an alkyl group having 1 to 8 carbon atoms, and a carbon number
  • Haloalkyl group of! ⁇ 8 haloalkoxyl group of 1-8 carbon atoms, alkylamino group of 1-8 carbon atoms, or dialkylamino group of 2-8 carbon atoms (the alkyl groups are bonded to each other to form a nitrogen atom) And may not form a halogen structure, an alkyl group, a haloalkyl group, a haloalkoxyl group, an anolenoquinamino group, or a dialkylamino group.
  • a hydrogen atom is preferred.
  • the compound preferably has a finer alignment structure.
  • any one of R to R is a fluorine atom, a cyan group, a trif
  • a chloromethyl group or a pentafluoroethyl group is preferred as a material for an n-type transistor.
  • the compound represented by the general formula (1) is a compound represented by the following general formula (5), a linear and dense alignment structure is preferable. Masle.
  • R 1 to R 5 are each independently a hydrogen atom, halogen atom, carbon
  • R to R and R to R are adjacent to each other to form a saturated cyclic structure.
  • R to R each independently represent a hydrogen atom, a carbon number
  • Alkyl group carbon number 1-30 haloalkyl group, carbon number 1-30 alkoxy group, carbon number 1-30 haloalkoxyl group, carbon number;! -30 alkylthio group, carbon number;! -30 halo
  • An alkylsilyl group of 1 to 30 or a cyan group is preferred.
  • the force S for giving specific examples of the compounds represented by the general formulas (1), (4) and (5) used for the organic semiconductor layer of the organic thin film transistor of the present invention is not limited thereto.
  • an electronic device such as the organic thin film light-emitting transistor of the present invention
  • purification by techniques such as column chromatography, recrystallization, distillation, and sublimation as necessary.
  • the performance and the on / off ratio can be increased to bring out the performance inherent in the material.
  • the organic thin film transistor of the present invention As an element configuration of the organic thin film transistor of the present invention, at least three terminals of a gate electrode, a source electrode, and a drain electrode, an insulator layer, and an organic semiconductor layer are provided on a substrate, and a voltage between the source and drain is applied to the gate electrode.
  • the thin film transistor As long as the thin film transistor is controlled by this, it is not limited and may have a known element structure.
  • elements A to D are shown in FIGS. 1 to 4 as typical element configurations of organic thin film transistors.
  • FIGS. 1 to 4 As described above, several configurations are known depending on the position of the electrode, the stacking order of the layers, and the like, and the organic thin film transistor of the present invention has a field effect transistor (FET) structure.
  • FET field effect transistor
  • An organic thin film transistor has an organic semiconductor layer (organic compound layer), a source electrode and a drain electrode formed so as to face each other with a predetermined distance from each other, and a predetermined distance from the source electrode and the drain electrode.
  • the current flowing between the source and drain electrodes is controlled by applying a voltage to the gate electrode.
  • the distance between the source electrode and the drain electrode is determined by the use of the organic thin film transistor of the present invention, and is usually 0 ⁇ 111 to 1111111, preferably 1111 to 100 ⁇ m, more preferably 5 ⁇ m. ⁇ 100 ⁇ m.
  • the organic thin film transistor of the element B has a gate electrode and an insulator layer in this order on a substrate. On the layer, there is a pair of source and drain electrodes formed at a predetermined interval, and an organic semiconductor layer is formed thereon. The organic semiconductor layer forms a channel region, and the on / off operation is performed by controlling the current flowing between the source electrode and the drain electrode with the voltage applied to the gate electrode.
  • the substrate in the organic thin film transistor of the present invention plays a role of supporting the structure of the organic thin film transistor.
  • inorganic compounds such as metal oxides and nitrides, plastic films (PET, PES, PC) ), Metal substrates, or composites or stacks thereof can also be used.
  • PET, PES, PC plastic films
  • Metal substrates, or composites or stacks thereof can also be used.
  • a silicon (Si) wafer is often used as a substrate material.
  • Si itself can be used as a gate electrode / substrate. It is also possible to oxidize the Si surface to form SiO and use it as an insulating layer.
  • a metal layer such as Au may be deposited on the Si substrate as the substrate and gate electrode as an electrode for connecting the lead wire.
  • Figure 8 shows an example of the element structure of an organic thin film transistor using a Si substrate.
  • the material for the gate electrode, the source electrode, and the drain electrode is not particularly limited as long as it is a conductive material.
  • the source electrode and the drain electrode those formed using a fluid electrode material such as a solution, paste, ink, or dispersion containing the above conductive material can be used.
  • the solvent or dispersion medium is preferably a solvent or dispersion medium containing 60% by mass or more, preferably 90% by mass or more of water, in order to suppress damage to the organic semiconductor.
  • a dispersion containing metal fine particles for example, a known conductive paste may be used, but a dispersion containing metal fine particles usually having a particle size of 0.5 nm to 50 nm, 1 nm to Onm. Preferably there is.
  • Examples of the material for the fine metal particles include platinum, gold, silver, nickel, chromium, copper, iron, tin, antimony lead, tantalum, indium, palladium, tellurium, rhenium, iridium, aluminum, ruthenium, genoremanium, and molybdenum. , Tungsten, zinc, or the like can be used.
  • an electrode using a dispersion in which these metal fine particles are dispersed in water or a dispersion medium which is an arbitrary organic solvent using a dispersion stabilizer mainly composed of an organic material.
  • a method for producing such a dispersion of metal fine particles metal ions in the liquid phase such as a physical generation method such as gas evaporation method, sputtering method, metal vapor synthesis method, colloid method, and coprecipitation method are used.
  • a chemical production method in which metal fine particles are produced by reduction preferably, JP-A-11-76800, JP-A-11-80647, JP-A-11-319538, JP-A-11-319538
  • the electrode After forming the electrode using these metal fine particle dispersions and drying the solvent, it is shaped as necessary in the range of 100 ° C to 300 ° C, preferably 150 ° C to 200 ° C. By heating, the metal fine particles are thermally fused to form an electrode pattern having a desired shape.
  • the gate electrode, the source electrode, and the drain electrode it is introduced by doping or the like. It is also preferable to use a known conductive polymer with improved electric conductivity, for example, conductive polyaniline, conductive polypyrrole, conductive polythiophene (polyethylenedioxythiophene and polystyrenesulfonic acid complex, etc.), polyethylene A complex of dioxythiophene (PEDOT) and polystyrene sulfonic acid is also preferably used. These materials can reduce the contact resistance between the source electrode and the organic semiconductor layer of the drain electrode.
  • a known conductive polymer with improved electric conductivity for example, conductive polyaniline, conductive polypyrrole, conductive polythiophene (polyethylenedioxythiophene and polystyrenesulfonic acid complex, etc.), polyethylene A complex of dioxythiophene (PEDOT) and polystyrene sulfonic acid is also preferably used. These materials can reduce the contact resistance between the
  • the material for forming the source electrode and the drain electrode is preferably a material having a small electric resistance at the contact surface with the organic semiconductor layer among the examples described above.
  • the electric resistance corresponds to the field-effect mobility when the current control device is manufactured.
  • the resistance should be as small as possible. This is generally determined by the magnitude relationship between the work function of the electrode material and the energy level of the organic semiconductor layer.
  • the work function (W) of the electrode material is a
  • the ionization potential of the organic semiconductor layer is (Ip) b
  • the electron affinity (Af) of the organic semiconductor layer is c
  • a, b, and c are all positive values based on the vacuum level.
  • b ⁇ a ⁇ l.5 eV (formula (1)) is preferable, and b ⁇ a ⁇ l.OeV is more preferable. If the above relationship can be maintained in relation to the organic semiconductor layer, it is preferable to select a material with a work function that is as large as possible, especially the work function of the electrode material.
  • the work function is more preferably 4.2 eV or more.
  • noble metals Al, Au, Cu, Pt
  • conductive polymers such as ITO, polyaniline and PEDOT: PSS and carbon are preferred. Even if the electrode material contains one or more of these high work function substances, there is no particular limitation as long as the work function satisfies the above formula (I).
  • a-c is preferably 1.5eV (formula ( ⁇ )), and more preferably a-c ⁇ l.OeV.
  • the work function of the electrode material is preferably as small as possible.
  • the work function is preferably 4.3 eV or less. More preferably, the work function is 3.7 eV or less.
  • low work function metals include, for example, an effective metal with a work function of 4.3 eV or less as described in Chemical Handbook II, page 493 (revised 3 edition, published by Maruzen Co., Ltd., 1983). It can be selected from the above list of Ag (4.26 eV), Al (4.06, 4.28 eV), Ba (2.52 eV), Ca (2.9 eV), Ce (2.9 eV), Cs (l.
  • the electrode material Even if one or more of these low work function substances are included as the electrode material, there is no particular limitation as long as the work function satisfies the above formula ( ⁇ ).
  • a stable metal in the air such as Ag or Au, if necessary.
  • the film thickness required for the coating must be 10 nm or more, and the power to protect from oxygen and water as the film thickness increases. For practical reasons, it is desirable to reduce it to 1 m or less for reasons such as increasing productivity! / ,.
  • Examples of the method for forming the electrode include vapor deposition, electron beam vapor deposition, sputtering, atmospheric pressure plasma method, ion plating, chemical vapor deposition, electrodeposition, electroless plating, spin coating, printing, and inkjet. Formed by means. Also if necessary As a method of turning, a conductive thin film formed by using the above method is formed by an electrode using a known photolithographic method or a lift-off method, by thermal transfer or ink jet on a metal foil such as aluminum or copper. There is a method of forming and etching a resist.
  • a conductive polymer solution or dispersion, a dispersion containing metal fine particles, or the like may be directly patterned by an ink-jet method, and may be formed by lithography, laser ablation, or the like from a coating film.
  • a method of patterning a conductive ink or conductive paste containing a conductive polymer or metal fine particles by a printing method such as relief printing, intaglio printing, planographic printing or screen printing.
  • the thickness of the thus formed electrode is not particularly limited as long as the conduction of current, preferably 0. 2nm ⁇ 10 i um, more preferably in the range of 4Nm ⁇ 300nm. Within this preferred range, the thin film thickness does not cause a voltage drop due to an increase in resistance. In addition, since the film is not too thick, it does not take time to form the film, and when another layer such as a protective layer or an organic semiconductor layer is laminated, the laminated film can be made smoothly without causing a step.
  • a buffer layer may be provided between the organic semiconductor layer and the source and drain electrodes for the purpose of improving the injection efficiency.
  • the noffer layer is a compound with an alkali metal or alkaline earth metal ion bond such as LiF, Li 0, CsF, NaCO, KC1, MgF, CaCO, etc. Is desirable.
  • a compound used as an electron injection layer or an electron transport layer in an organic EL device such as Alq (tris (8-quinolinol) ano-remium complex) may be inserted.
  • cyan compounds such as FeCl, TCNQ, F—TCNQ, HAT, CFx, GeO, SiO, MoO, V O, VO, V O, MnO, Mn O, ZrO
  • Alkali metals such as WO, TiO, InO, ZnO, NiO, HfO, TaO, ReO, PbO
  • Metal oxides other than alkaline earth metals and inorganic compounds such as ZnS and ZnSe are desirable. In many cases, these oxides cause oxygen vacancies, which are suitable for hole injection.
  • TPD N, ⁇ '-bis (3-methylphenyl) -1 N, ⁇ '-diphenyl-1- (1, 1'-biphenyl) -1,4'-diamin
  • NPD 4, 4'—Bis [N— (1-Naphthinole) -N-phenylamino] biphenyl
  • CuPc copper phthalocyanine
  • It may be a compound used as a hole injection layer or a hole transport layer in the element. In addition, it would be desirable to have two or more of the above compounds.
  • the power of the nofer layer is known to have the effect of lowering the threshold voltage by lowering the carrier injection barrier and driving the transistor at a low voltage. It has been found that there is an effect of improving mobility. This is because a carrier trap exists at the interface between the organic semiconductor and the insulator layer, and when carrier injection occurs when a gate voltage is applied, the first injected carrier is used to fill the trap.
  • the buffer layer is required to be thin between the electrode and the organic semiconductor layer, and its thickness is 0.1 nm to 30 nm, preferably 0.3 nm to 20 nm.
  • the material of the insulator layer in the organic thin film transistor of the present invention is not particularly limited as long as it has an electrical insulating property and can be formed as a thin film.
  • Metal oxide including silicon oxide
  • metal nitride Materials having a resistivity of 10 ⁇ cm or more at room temperature, such as silicon nitride
  • polymers such as polymers, and small organic molecules
  • inorganic oxide films having a high relative dielectric constant are particularly preferable.
  • inorganic oxides include silicon oxide, aluminum oxide, tantalum oxide, titanium oxide, tin oxide, vanadium oxide, barium strontium titanate, sodium zirconate titanate, lead zirconate titanate, lead lanthanum titanate, titanate Strontium, barium titanate, barium magnesium fluoride, lanthanum oxide, fluorine oxide, magnesium oxide, bismuth oxide, bismuth titanate, niobium oxide, strontium bismuth titanate, strontium bismuth tantalate, pentoxide Tantanole, bismuth tantalate niobate, yttrium trioxide, and combinations thereof, including silicon oxide, aluminum oxide, tantalum oxide, and titanium oxide are preferred.
  • inorganic nitrides such as silicon nitride (SiN, SixNy (x, y> 0)), aluminum nitride, etc.
  • the insulator layer may be formed of a precursor containing an alkoxide metal.
  • a substrate is coated with a solution of the precursor, and this is subjected to chemical solution treatment including heat treatment. By doing so, an insulator layer is formed.
  • the metal in the alkoxide metal is selected from, for example, a transition metal, a lanthanoid, or a main group element.
  • the metal is tantalum (Ba), strontium (Sr), titanium (Ti), bismuth (Bi), tantalum.
  • Ti zircon
  • Zr iron
  • Fe nickel
  • Mn manganese
  • lead Pb
  • La lithium
  • Li lithium
  • Na sodium
  • K Norebidium
  • Cs cesium
  • Be beryllium
  • Mg magnesium
  • Ca calcium
  • Ca niobium
  • T1 mercury
  • Hg mercury
  • Cu copper
  • Co Cobalt
  • Co rhodium
  • Sc scandium
  • Y yttrium
  • alkoxide in the alkoxide metal examples include, for example, alcohols including methanol, ethanol, propanol, isopropanol, butanol, isobutanol, methoxy ethanol, ethoxy ethanol, propoxy ethanol, butoxy ethanol, pentoxy ethanol. , Heptoxy ethanol, methoxypropanol, ethoxypropanol, propoxypropanol, butoxypropanol, pentoxypropanol, and alkoxy alcohols including heptoxypropanol. .
  • the insulator layer is made of the material as described above, polarization is likely to occur in the insulator layer, and the threshold voltage for transistor operation can be reduced.
  • insulating with silicon nitride such as SiN, SixNv, SiONx (x, y> 0)
  • Insulator layers using organic compounds include polyimides, polyamides, polyesters, polyacrylates, photo-radical polymerization systems, photo-curing resins based on photothion polymerization, copolymers containing acrylonitrile components, polybutanol, poly-polyphenol. Bull alcohol, nopolac resin, cyano ethyl pullulan and the like can also be used.
  • wax polyethylene, polychloropyrene, polyethylene terephthalate, polyoxymethylene, polybutyl chloride, polyvinylidene fluoride, polymethylmetatalylate, polysanolone, polycarbonate, polyimide cyanoethynolef.
  • Norelan poly (vinino fenenore) (PVP), poly (methyl methacrylate) (PMMA), polycarbonate (PC), polystyrene (PS), polyolefin, polyacrylamide, poly (acrylic acid), nopolac resin, resole
  • PVP poly (vinino fenenore)
  • PMMA poly (methyl methacrylate)
  • PC polycarbonate
  • PS polystyrene
  • polyolefin polyacrylamide
  • poly (acrylic acid) nopolac resin
  • resole In addition to resin, polyimide, polyxylylene, and epoxy resin, it is also possible to use a polymer material having a high dielectric constant such as pullulan.
  • an organic compound having water repellency is particularly preferable.
  • the water repellency suppresses the interaction between the insulator layer and the organic semiconductor layer, and the organic semiconductor Utilizing the inherent cohesion, the crystallinity of the organic semiconductor layer can be increased to improve device performance. Examples of this include polyparaxylylene derivatives described in Yasud a et al. Jpn. J. Appl. Phys. Vol. 42 (2003) pp. 6614-6618 and Janos Veres et al. Chem. Mater., Vol. 16 (2004) pp. 4543-4555.
  • the organic semiconductor layer can be formed with less damage. It is an effective method because it can.
  • the insulator layer may be a mixed layer using a plurality of inorganic or organic compound materials as described above, or may be a laminated structure thereof.
  • the device performance can be controlled by mixing or laminating materials with high dielectric constant, materials and water repellency, if necessary.
  • the insulator layer may include an anodized film or the anodized film as a component.
  • the anodized film is preferably sealed.
  • the anodized film is formed by anodizing a metal that can be anodized by a known method. Examples of the metal that can be anodized include aluminum and tantalum, and a known method without particular limitation can be used for the method of anodizing.
  • An oxide film is formed by anodizing. Any electrolyte solution that can form a porous oxide film can be used as the anodizing treatment.
  • sulfuric acid, phosphoric acid, oxalic acid, chromic acid, boric acid, sulfamic acid, benzenesulfone, and the like can be used. Acids, etc., or mixed acids obtained by combining two or more of these or salts thereof are used.
  • the treatment conditions for anodization vary depending on the electrolyte used, so it cannot be specified in general, but in general, the electrolyte concentration is;! ⁇ 80 mass%, electrolyte temperature 5 ⁇ 70 ° C A current density of 0.5 to 60 A / cm 2 , a voltage of 1 to 100 volts, and an electrolysis time of 10 seconds to 5 minutes are suitable.
  • the oxidation treatment is a method in which an aqueous solution of sulfuric acid, phosphoric acid or boric acid is used as the electrolytic solution and the treatment is performed with a direct current, but an alternating current can also be used.
  • the concentration of these acids is preferably 5 to 45% by weight. It is preferable to perform electrolytic treatment for 20 to 250 seconds at an electrolyte temperature of 20 to 50 ° C and a current density of 0.5 to 20 A / cm 2. Better!/,.
  • the thickness of the insulator layer if the layer thickness is small, the effective voltage applied to the organic semiconductor increases, so that the drive voltage and threshold voltage of the device itself can be lowered. Since the current increases, it is necessary to select an appropriate film thickness, usually 10 nm to 5 ⁇ m, preferably 50 nm to 2 ⁇ m, and more preferably lOOnm to ⁇ ⁇ m 3 ⁇ 4> ⁇ ⁇ .
  • an arbitrary orientation treatment may be performed between the insulator layer and the organic semiconductor layer.
  • it is a method for improving the crystallinity of the organic semiconductor layer by reducing the interaction between the insulator layer and the organic semiconductor layer by applying a water repellent treatment to the surface of the insulator layer.
  • silane coupling agents such as octadecyltrichlorosilane, trichloromethylsilazane, self-anchored alignment film materials such as anolecanic acid, anolecansnorephonic acid, and ananolecan-powered norevonic acid are used.
  • a self-organized film is formed by contacting with the surface of the insulating film and then appropriately dried.
  • a method in which a film made of polyimide or the like is placed on the surface of the insulating film and the surface is rubbed so as to be used for liquid crystal alignment is also preferable.
  • the insulator layer may be formed by vacuum deposition, molecular beam epitaxy, ion cluster beam, low energy ion beam, ion plating, CV D, sputtering, 11-61406, 11-133205, JP-A 2000-121804, 2000-147209, 2000-185362, dry process such as atmospheric pressure plasma method, spray coating method, Wet processes such as spin coating, blade coating, dip coating, casting, roll coating, bar coating, die coating, and other wet processes such as printing and ink jet patterning Can be used according to.
  • the wet process includes a method in which fine particles of inorganic oxide are dispersed in an arbitrary organic solvent or water using a dispersion aid such as a surfactant as required, and dried, or an oxide precursor
  • a so-called sol-gel method in which an alkoxide solution is applied and dried is used.
  • the thickness of the organic semiconductor layer in the organic thin film transistor of the present invention is not particularly limited, but is usually from 0.511 to 1111, and preferably from 2 to 250 nm.
  • the formation method of the organic semiconductor layer is not particularly limited, and a known method can be applied.
  • a known method can be applied.
  • MBE molecular beam vapor deposition
  • vacuum vapor deposition chemical vapor deposition
  • dipping of a solution in which a material is dissolved in a solvent Printing, spin coating method, casting method, bar coating method, mouth coating method, etc., coating method and baking, elect mouth polymer line determination, molecular beam deposition, self-assembly from solution, and combinations thereof
  • it is formed of the material of the organic semiconductor layer as described above.
  • the substrate temperature during film formation is preferably 50 to 250 ° C, more preferably 70 to 150 ° C.
  • the annealing temperature is preferably 50 to 200 ° C, more preferably 70 to 200 ° C, and the time is preferably 10 minutes to 12 hours; more preferably 10 to 12 hours.
  • the organic semiconductor layer may be a combination of a plurality of materials selected from the general formulas (1) to (4), or a known semiconductor such as pentacene or thiophene oligomer. It can be used with multiple mixed thin films or stacked layers.
  • the method for forming the organic thin film transistor of the present invention is not particularly limited and may be a known method. According to a desired element configuration, the substrate is charged, the gate electrode is formed, the insulator layer is formed, the organic semiconductor layer is formed, and the source electrode is formed. It is preferable to form a series of device fabrication steps up to the formation of the drain electrode without being exposed to the atmosphere at all, because it is possible to prevent the device performance from being hindered by moisture or oxygen in the atmosphere due to contact with the atmosphere. If it is unavoidable that the atmosphere must be exposed to the atmosphere once, the steps after the organic semiconductor layer deposition should not be exposed to the atmosphere at all.
  • the surface where the source electrode and drain electrode are partially laminated on the insulating layer is cleaned and activated by ultraviolet irradiation, ultraviolet / ozone irradiation, oxygen plasma, argon plasma, etc., and then the organic semiconductor layer Are preferably laminated.
  • a gas barrier layer may be formed on the whole or a part of the outer peripheral surface of the organic transistor element.
  • the material for forming the gas noble layer those commonly used in this field can be used.
  • Examples thereof include polybutyl alcohol, ethylene butyl alcohol copolymer, polyvinyl chloride, polyvinylidene chloride, and polychlorotrifluoroethylene. Can be mentioned. Furthermore, insulating inorganic materials exemplified for the insulator layer can also be used.
  • the present invention also provides an organic thin film light emitting transistor in which light emission is obtained by using a current flowing between a source and a drain in the organic thin film transistor, and the light emission is controlled by applying a voltage to a gate electrode.
  • the organic thin film transistor can also be used as a light emitting device using charges injected from the source and drain electrodes. That is, the organic thin film transistor can be used as an organic thin film light emitting transistor that also functions as a light emitting element (organic EL element). This can control the light emission intensity by controlling the current flowing between the source and drain electrodes with the gate electrode. Since the transistor for controlling light emission and the light emitting element can be integrated, it is possible to reduce the cost by improving the aperture ratio of the display and simplifying the manufacturing process, which provides a great practical advantage.
  • the contents described in the detailed description above are sufficient, but in order to operate the organic thin film transistor of the present invention as an organic light-emitting transistor, holes are generated from one of the source and the drain and from the other. Electrons must be injected, and the following conditions are preferably satisfied in order to improve the light emission performance.
  • a hole injection electrode is an electrode containing a substance having a work function of 4.2 eV or higher.
  • An electron injecting electrode is an electrode containing a substance having a work function of 4.3 eV or less. More preferably, it is an organic thin film light-emitting transistor provided with an electrode in which one is hole-injecting and the other is electron-injecting.
  • the organic thin film light-emitting transistor of the present invention it is preferable to insert a hole injection layer between at least one electrode and the organic semiconductor layer in order to improve the hole injection property.
  • the hole injection layer include amine-based materials used as hole injection materials and hole transport materials in organic EL devices.
  • the electron injection layer used for organic EL devices can be used for the electron injection layer.
  • it is an organic thin film light emitting transistor comprising a hole injection layer under one electrode and an electron injection layer under the other electrode.
  • a buffer layer may be provided between the organic semiconductor layer and the source and drain electrodes for the purpose of improving the injection efficiency.
  • the compound (1) was synthesized as follows. The synthesis route is shown below.
  • the compound was purified by sublimation at 220 ° C.
  • the purity of the compound (1) obtained by sublimation purification was 99.5%.
  • HX110 manufactured by JEOL Ltd.
  • An organic thin film transistor was produced by the following procedure. First, the surface of a Si substrate (also used as a P-type specific resistance 1 ⁇ cm gate electrode) was oxidized by thermal oxidation, and a 300 nm thermal oxide film was formed on the substrate to form an insulator layer. Furthermore, after the SiO film deposited on one side of the substrate is completely removed by dry etching, chromium is deposited to a thickness of 20 nm by sputtering, and further gold (Au) is deposited by lOOnm sputtering. A film was taken out and used as an electrode. This substrate was subjected to ultrasonic cleaning with a neutral detergent, pure water, acetone and ethanol for 30 minutes each, followed by ozone cleaning.
  • a neutral detergent, pure water, acetone and ethanol for 30 minutes each, followed by ozone cleaning.
  • the above substrate was installed in a vacuum deposition apparatus (ULVAC, EX-400), and the same procedure was performed except that etyltoluene was used on the insulator layer in place of the ethylbenzene used in Synthesis Example 1.
  • the compound (2) synthesized as described above was formed as an organic semiconductor layer having a thickness of 50 ⁇ m at a deposition rate of 0.05 nm / s.
  • gold was deposited to a thickness of 50 nm through a metal mask to form a source electrode and a drain electrode that were not in contact with each other so that the distance (channel length U was 75 m.
  • the source electrode and the drain electrode An organic thin film transistor was fabricated by depositing the electrode so that the width (channel width W) was 5 mm (see Fig. 7). A gate voltage of 40 V was applied to the gate electrode of the obtained organic thin film transistor, and a current was applied by applying a voltage between the source and drain. In this case, electrons are induced in the channel region (between source and drain) of the organic semiconductor layer and operate as a p-type transistor. As a result, the on / off ratio of the current between the source and drain electrodes in the current saturation region was 3 ⁇ 10 5 . Further, the hole of the field-effect mobility was 3 X 10- 2 cm 2 ZVs was calculated by the following formula (A).
  • I is the source-drain current
  • W is the channel width
  • L is the channel length
  • C is the gain
  • V Capacitance per unit area of the gate insulator layer
  • V is the gate threshold voltage
  • V is the gate voltage
  • Example 1 an organic thin film transistor was fabricated in the same manner except that the compound shown in Table 1 was used instead of the compound (2) as the material of the organic semiconductor layer.
  • the obtained organic thin film transistor was p-type at a gate voltage of 40 V in the same manner as in Example 1.
  • Table 1 shows the results of measuring the field effect mobility of holes by measuring the on / off ratio of the current between the source and drain electrodes.
  • Example 1 the organic semiconductor layer was similarly formed except that the compound (110) was used instead of the compound (2) as the material of the organic semiconductor layer.
  • the compound (110) was used instead of the compound (2) as the material of the organic semiconductor layer.
  • Ca was vacuum-deposited at a deposition rate of 0.05 nm / s to 20 nm, and then Ag was deposited at a deposition rate of 0.05 nm / s to 50 nm to coat Ca.
  • An organic thin film transistor was fabricated. The obtained organic thin film transistor was n-type driven at a gate voltage V of + 40V. Measure the on / off ratio of the current between the source and drain electrodes.
  • Table 1 shows the results of calculating the field-effect mobility of electrons and electrons.
  • Example 8 an organic thin film transistor was prepared in the same manner except that the compound (44) was used instead of the compound (110) as the material of the organic semiconductor layer.
  • the obtained organic thin film transistor was driven n-type at a gate voltage V of +40 V in the same manner as in Example 8.
  • Table 1 shows the results of measuring the on / off ratio of the current between the source and drain electrodes and calculating the electron field-effect mobility.
  • Example 6 instead of Au alone as a source / drain electrode, buffer layer MoO
  • An organic thin film transistor was fabricated in the same manner except that 3 was vacuum deposited at a deposition rate of 0.05 nm / s for 10 nm and inserted between a thin film of Au and compound (61). The obtained organic thin film transistor was p-type driven at a gate voltage V of 40 V in the same manner as in Example 1.
  • the glass substrate was ultrasonically cleaned with a neutral detergent, pure water, acetone, and ethanol for 30 minutes each, and then a gold (Au) film of 40 nm was formed by sputtering to produce a gate electrode.
  • this substrate was set in a film forming section of a thermal CVD apparatus.
  • 250 mg of polyparaxylene derivative [polyparaxylene chloride (Parylene)] (trade name; diX-C, manufactured by Sansei Kasei Co., Ltd.), which is the raw material for the insulator layer, is placed in a petri dish. Vacuum the thermal CVD device with a vacuum pump and reduce the pressure to 5 Pa. Then, heat the evaporation part to 180 ° C and the polymerization part to 680 ° C and leave it for 2 hours. A layer was formed.
  • the gate electrode of the obtained organic thin film transistor was p-type driven at a gate voltage V of ⁇ 40V. Measure the on / off ratio of the current between the source and drain electrodes.
  • Table 1 shows the results of the calculation of the field effect mobility of holes.
  • Example 11 instead of the compound (60), the compound (60 An organic thin film transistor was fabricated in the same manner except that 61) was used. The obtained organic thin film transistor was p-type driven at a gate voltage V of 40 V in the same manner as in Example 1.
  • Table 1 shows the results of measuring the field-effect mobility of holes by measuring the on / off ratio of the current between the source and drain electrodes.
  • Example 11 an organic thin film transistor was produced in the same manner except that the compound (44) was used instead of the compound (60) as the material of the organic semiconductor layer.
  • the obtained organic thin film transistor was driven n-type at a gate voltage V of +40 V in the same manner as in Example 8.
  • Table 1 shows the results of measuring the on / off ratio of the current between the source and drain electrodes and calculating the electron field-effect mobility.
  • Example 11 an organic thin film transistor was produced in the same manner except that the compound (65) was used instead of the compound (60) as the material of the organic semiconductor layer.
  • the obtained organic thin film transistor was driven n-type at a gate voltage V of +40 V in the same manner as in Example 8.
  • Table 1 shows the results of measuring the on / off ratio of the current between the source and drain electrodes and calculating the electron field-effect mobility.
  • Example 11 the substrate was cleaned, the gate electrode was formed, and the insulator layer was formed. Next, 0.5% by weight of Compound (175) was dissolved in black mouth form, and the film was formed on the substrate on which the insulator layer was formed with a spin coater (Mikasa Co., Ltd .: 1H-D7), and a nitrogen atmosphere. The film was dried at 80 ° C. to form an organic semiconductor layer. Next, by depositing gold (Au) with a film thickness of 50 nm through a metal mask with a vacuum deposition apparatus, source and drain electrodes that were not in contact with each other were formed to produce an organic thin film transistor.
  • Au gold
  • the obtained organic thin film transistor was p-type driven at a gate voltage V of 40 V in the same manner as in Example 1. Measure the on / off ratio of the current between the source and drain electrodes,
  • Table 1 shows the results of calculating the field-effect mobility ⁇ of holes.
  • PV Polyparaphenylenevinylene
  • the obtained organic thin film transistor was p-type driven at a gate voltage V of 40 V in the same manner as in Example 1. Measure the on / off ratio of the current between the source and drain electrodes,
  • Table 1 shows the results of the calculation of the field effect mobility ⁇ of holes and holes.
  • Polyparaphenylenevinylene (PPV) was used as the material for the organic semiconductor layer, and the organic semiconductor layer was formed in exactly the same manner as in Comparative Example 1. Thereafter, an organic thin film transistor obtained by depositing Ca as a source / drain electrode through a metal mask in the same manner as in Example 8 and coating Ag thereon is obtained in the same manner as in Example 8. N-type drive was performed at a gate voltage V of 40V. Measure the on / off ratio of the current between the source and drain electrodes,
  • Table 1 shows the results of the calculation of the field effect mobility ⁇ of holes and holes.
  • An organic thin film light emitting transistor was produced by the following procedure. First, the surface of a Si substrate (also used as a P-type specific resistance 1 ⁇ cm gate electrode) was oxidized by a thermal oxidation method, and a 300 nm thermal oxide film was formed on the substrate to form an insulator layer. Furthermore, after the SiO film deposited on one side of the substrate is completely removed by dry etching, chromium is deposited to a thickness of 20 nm by sputtering, and further gold (Au) is deposited by lOOnm sputtering. A film was taken out and used as an electrode. This substrate was ultrasonically cleaned with a neutral detergent, pure water, acetone and ethanol for 30 minutes each.
  • the organic thin film transistor of the present invention has a high response speed (driving speed) by using a compound having a specific structure having high electron mobility as a material for the organic semiconductor layer, It has a high performance as a transistor with a large on / off ratio and can be used as an organic thin film light emitting transistor capable of emitting light.

Abstract

La présente invention concerne un transistor organique à couche mince dans lequel au moins trois bornes, c'est-à-dire une électrode de gâchette, une électrode source et une électrode de drain, une couche isolante et une couche semi-conductrice organique sont disposées sur un substrat, et dont le courant source-drain est commandé en appliquant une tension à l'électrode de gâchette. Dans ce transistor organique à couche mince, la couche semi-conductrice organique contient un composé comportant une structure spécifique. L'invention concerne également un transistor organique à couche mince émetteur de lumière dans lequel l'émission de lumière est obtenue en utilisant le courant entre la source et le drain d'un transistor organique à couche mince, tout en contrôlant l'émission de lumière en appliquant une tension à l'électrode de gâchette. Le transistor organique à couche mince présente une vitesse de réponse élevée (vitesse d'excitation) et un rapport de résistance élevé. Le transistor organique à couche mince émetteur de lumière utilise un tel transistor organique à couche mince.
PCT/JP2007/069729 2006-10-12 2007-10-10 Dispositif de transistor organique à couche mince et transistor organique à couche mince émetteur de lumière WO2008044695A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2008538733A JP5368797B2 (ja) 2006-10-12 2007-10-10 有機薄膜トランジスタ素子及び有機薄膜発光トランジスタ
EP07829467A EP2073290A4 (fr) 2006-10-12 2007-10-10 Dispositif de transistor organique à couche mince et transistor organique à couche mince émetteur de lumière
US12/445,146 US8217389B2 (en) 2006-10-12 2007-10-10 Organic thin film transistor device and organic thin film light-emitting transistor
CN200780037982XA CN101523631B (zh) 2006-10-12 2007-10-10 有机薄膜晶体管元件以及有机薄膜发光晶体管

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006-278643 2006-10-12
JP2006278643 2006-10-12

Publications (1)

Publication Number Publication Date
WO2008044695A1 true WO2008044695A1 (fr) 2008-04-17

Family

ID=39282888

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/069729 WO2008044695A1 (fr) 2006-10-12 2007-10-10 Dispositif de transistor organique à couche mince et transistor organique à couche mince émetteur de lumière

Country Status (7)

Country Link
US (1) US8217389B2 (fr)
EP (1) EP2073290A4 (fr)
JP (1) JP5368797B2 (fr)
KR (1) KR20090077779A (fr)
CN (1) CN101523631B (fr)
TW (1) TW200835009A (fr)
WO (1) WO2008044695A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009125721A1 (fr) * 2008-04-10 2009-10-15 出光興産株式会社 Composé chimique utilisé pour un transistor organique en couches minces et transistor organique en couches minces
WO2011036866A1 (fr) * 2009-09-25 2011-03-31 出光興産株式会社 Transistor en film organique mince
WO2011065015A1 (fr) * 2009-11-30 2011-06-03 出光興産株式会社 Composition contenant un matériau semi-conducteur organique, et transistor à film mince organique utilisant ladite composition
WO2011087130A1 (fr) * 2010-01-18 2011-07-21 株式会社クラレ Composé acétylénique et matériau semi-conducteur organique le comportant
DE102011119293A1 (de) 2011-01-10 2012-07-12 Merck Patent Gmbh Verbindungen für ein flüssigkristallines Medium und deren Verwendung für Hochfrequenzbauteile
JP2013033823A (ja) * 2011-08-01 2013-02-14 National Institute Of Advanced Industrial & Technology 有機半導体材料
JP2013035814A (ja) * 2011-08-11 2013-02-21 Ricoh Co Ltd 新規な有機半導体材料およびそれを用いた電子デバイス
JP2013508317A (ja) * 2009-10-24 2013-03-07 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶媒体のための化合物および高周波構成要素のための使用
JP2013510101A (ja) * 2009-11-04 2013-03-21 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶媒体のための化合物および高周波構成要素のためのその使用
JP2018513836A (ja) * 2015-02-26 2018-05-31 ソニー株式会社 フェニルエチニルナフタレン染料およびそれらの使用方法

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101300006B1 (ko) * 2006-09-28 2013-08-26 주식회사 동진쎄미켐 전자 소자용 화합물 및 이를 포함하는 전자 소자
JP2011044686A (ja) * 2009-07-22 2011-03-03 Ricoh Co Ltd 新規な有機半導体材料とそれを用いた電子デバイス
WO2011055529A1 (fr) 2009-11-05 2011-05-12 出光興産株式会社 Composé aromatique asymétrique contenant un hétérocycle, composé pour un transistor organique en couches minces, et transistor organique en couches minces l'utilisant
CN102971283A (zh) * 2010-07-08 2013-03-13 旭硝子株式会社 含氟芳香族化合物、有机半导体材料和有机薄膜器件
WO2012068744A1 (fr) * 2010-11-26 2012-05-31 海洋王照明科技股份有限公司 Dispositif électroluminescent organique et procédé de fabrication correspondant
DE102011119900A1 (de) * 2011-01-21 2012-07-26 Merck Patent Gmbh Flüssigkristalline Medien, Bauteile für die Hochfrequenztechnik und mesogene Verbindungen
WO2012126570A1 (fr) 2011-03-22 2012-09-27 Merck Patent Gmbh Composés pour un milieu cristallin liquide et leur utilisation pour des composants haute fréquence
WO2014044357A1 (fr) * 2012-09-21 2014-03-27 Merck Patent Gmbh Composés comprenant une triple liaison c-c et leur utilisation dans des mélanges de cristaux liquides
EP2966701B1 (fr) * 2013-03-07 2020-02-19 DIC Corporation Couche mince organique, dispositif semi-conducteur organique, et transistor organique l'utilisant
WO2015027176A1 (fr) 2013-08-22 2015-02-26 Sony Corporation Colorants colorés ou fluorescent hydrosolubles et procédés d'utilisation correspondants
EP3094687B1 (fr) 2014-01-16 2020-02-12 Sony Corporation Teintures colorées ou fluorescentes hydrosolubles
CN104073260A (zh) * 2014-05-28 2014-10-01 北京大学 萘系列高双折射率液晶化合物及其制备方法
US11827661B2 (en) 2015-02-26 2023-11-28 Sony Group Corporation Water soluble fluorescent or colored dyes comprising conjugating groups
KR20180005650A (ko) 2015-05-11 2018-01-16 소니 주식회사 초휘도 이량체성 또는 중합체성 염료
CN104851906B (zh) * 2015-05-15 2017-12-01 京东方科技集团股份有限公司 显示基板及其制作方法和驱动方法以及显示装置
CN108630820A (zh) * 2017-03-21 2018-10-09 北京大学深圳研究生院 一种交流平面有机电致发光器件
WO2017105470A1 (fr) * 2015-12-17 2017-06-22 Intel Corporation Dispositifs et interconnexions à base de graphène à faible teneur en défauts
CN105552242B (zh) * 2016-01-29 2017-05-03 苏州大学 一种用于半导体器件的双电荷注入层的制备方法
EP3436529A1 (fr) 2016-04-01 2019-02-06 Sony Corporation Colorants dimères ou polymères ultra-brillants
EP3436528A1 (fr) 2016-04-01 2019-02-06 Sony Corporation Colorants dimères ou polymères ultra-brillants à groupes d'espacement rigides
RU2753706C2 (ru) 2016-04-06 2021-08-20 Сони Корпорейшн Ультраяркие димерные или полимерные красители со спейсерными линкерными группами
EP3455238A1 (fr) 2016-05-10 2019-03-20 Sony Corporation Colorants polymères ultra-brillants à squelettes peptidiques
EP3455299B1 (fr) 2016-05-10 2024-01-17 Sony Group Corporation Compositions comprenant un colorant polymère et une cyclodextrine et leurs utilisations
CN109071961B (zh) 2016-05-11 2021-04-27 索尼公司 超亮二聚或聚合染料
EP3464477A1 (fr) 2016-06-06 2019-04-10 Sony Corporation Polymères ioniques comprenant des groupes rapporteurs fluorescents ou colorés
EP3691690A1 (fr) 2017-10-05 2020-08-12 Sony Corporation Médicaments polymères programmables
US11931419B2 (en) 2017-11-16 2024-03-19 Sony Group Corporation Programmable polymeric drugs
US11874280B2 (en) 2018-03-19 2024-01-16 Sony Group Corporation Use of divalent metals for enhancement of fluorescent signals
JP2021518410A (ja) 2018-03-21 2021-08-02 ソニーグループ株式会社 リンカー基を有するポリマータンデム色素
KR102486779B1 (ko) 2019-09-26 2023-01-12 소니그룹주식회사 링커 그룹을 갖는 중합체성 탠덤 염료
CN110911573B (zh) * 2019-11-29 2021-08-31 福州大学 一种提高发光效率的交流驱动有机发光场效应晶体管及其制备方法
CN111081740A (zh) * 2019-12-06 2020-04-28 深圳市华星光电半导体显示技术有限公司 一种显示面板

Citations (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0555568A (ja) 1991-08-28 1993-03-05 Asahi Chem Ind Co Ltd 有機薄膜トランジスタ
JPH08228035A (ja) 1994-12-09 1996-09-03 At & T Corp 薄膜トランジスタ装置とその製造方法
JPH08228034A (ja) 1994-12-09 1996-09-03 At & T Corp 有機薄膜トランジスタ装置
JPH09232589A (ja) 1996-01-29 1997-09-05 Motorola Inc 有機薄膜トランジスタ
JPH1019001A (ja) 1996-07-04 1998-01-20 Nhk Spring Co Ltd メタルベローズアキュムレータ
JPH10125924A (ja) 1996-10-17 1998-05-15 Matsushita Electric Ind Co Ltd 有機薄膜トランジスタ及び液晶素子と有機発光素子
JPH10135481A (ja) 1996-10-15 1998-05-22 Lucent Technol Inc 薄膜トランジスタからなるデバイス
JPH1161406A (ja) 1997-08-27 1999-03-05 Sekisui Chem Co Ltd 反射・帯電防止膜の製造方法
JPH1176800A (ja) 1997-07-17 1999-03-23 Nippon Paint Co Ltd 貴金属又は銅の固体ゾル及び製造方法並びに塗料組成物及び樹脂成型物
JPH1180647A (ja) 1997-07-17 1999-03-26 Nippon Paint Co Ltd 貴金属又は銅のコロイド溶液及びその製造方法並びに塗料組成物及び樹脂成型物
JPH11133205A (ja) 1997-04-21 1999-05-21 Sekisui Chem Co Ltd 反射防止膜の製造方法
JPH11251601A (ja) 1997-11-24 1999-09-17 Lucent Technol Inc 半導体デバイス
JPH11319538A (ja) 1998-05-20 1999-11-24 Nippon Paint Co Ltd 貴金属又は銅のコロイドの製造方法
JP2000123634A (ja) 1998-08-10 2000-04-28 Vacuum Metallurgical Co Ltd Ｃｕ超微粒子独立分散液
JP2000121804A (ja) 1998-10-09 2000-04-28 Sekisui Chem Co Ltd 反射防止フィルム
JP2000124157A (ja) 1998-08-10 2000-04-28 Vacuum Metallurgical Co Ltd Ｃｕ薄膜の形成法
JP2000147209A (ja) 1998-09-09 2000-05-26 Sekisui Chem Co Ltd 反射防止フィルム及びその製造方法
JP2000174277A (ja) 1998-12-01 2000-06-23 Hitachi Ltd 薄膜トランジスタおよびその製造方法
JP2000185362A (ja) 1998-12-24 2000-07-04 Sekisui Chem Co Ltd 金属元素含有薄膜積層体の製造方法
JP2000239853A (ja) 1999-02-25 2000-09-05 Nippon Paint Co Ltd 金属薄膜の形成方法及び反射型液晶表示装置用反射板の製造方法
JP2001035255A (ja) 1999-07-22 2001-02-09 Vacuum Metallurgical Co Ltd 銀超微粒子独立分散液
JP2001053028A (ja) 1999-08-11 2001-02-23 Vacuum Metallurgical Co Ltd Ｃｕ薄膜の形成法
JP2001094107A (ja) 1999-09-20 2001-04-06 Hitachi Ltd 有機半導体装置及び液晶表示装置
JP2001254185A (ja) 2000-03-13 2001-09-18 Vacuum Metallurgical Co Ltd 導電性金属薄膜の形成方法およびその方法に使用する導電性金属超微粒子分散物
JP2003073382A (ja) 2001-07-09 2003-03-12 Merck Patent Gmbh チエノチオフェン誘導体
JP2004179249A (ja) 2002-11-25 2004-06-24 Mitsubishi Chemicals Corp 有機半導体材料及びそれを用いた有機電子デバイス、及び有機電子デバイスの製造方法
JP2005244236A (ja) * 2004-02-24 2005-09-08 Hewlett-Packard Development Co Lp 双安定分子スイッチ及びそれに関連する方法
JP2007059682A (ja) * 2005-08-25 2007-03-08 Konica Minolta Holdings Inc 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ
JP2007238866A (ja) * 2006-03-10 2007-09-20 Ricoh Co Ltd π共役ポリマー
JP2007311608A (ja) * 2006-05-19 2007-11-29 Konica Minolta Holdings Inc 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6107117A (en) 1996-12-20 2000-08-22 Lucent Technologies Inc. Method of making an organic thin film transistor
US6207472B1 (en) * 1999-03-09 2001-03-27 International Business Machines Corporation Low temperature thin film transistor fabrication
AU2002227138A1 (en) 2000-10-24 2002-05-06 Molecular Electronics Corporation Three-terminal field-controlled molecular devices
JP3856202B2 (ja) * 2001-10-05 2006-12-13 日本電気株式会社 有機薄膜トランジスタ
JP3823312B2 (ja) * 2001-10-18 2006-09-20 日本電気株式会社 有機薄膜トランジスタ
WO2004018488A1 (fr) * 2002-08-23 2004-03-04 Japan Science And Technology Agency Materiau organique $g(p)-conjugue de type a anneau polycyclique fuse, ses intermediaires et son procede de production
DE602004028399D1 (de) * 2003-11-28 2010-09-09 Merck Patent Gmbh Organische halbleiterschicht-formulierungen mit polyacenen und organischen binderpolymeren
JP2005330185A (ja) * 2004-05-18 2005-12-02 Takasago Internatl Corp ジチア−ｓ−インダセン誘導体
KR100659061B1 (ko) * 2004-09-20 2006-12-19 삼성에스디아이 주식회사 유기 박막 트랜지스터 및 이를 구비한 평판표시장치
WO2007068618A1 (fr) 2005-12-12 2007-06-21 Ciba Holding Inc. Semi-conducteurs organiques et leur fabrication
JP2008078279A (ja) * 2006-09-20 2008-04-03 Konica Minolta Holdings Inc 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ

Patent Citations (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0555568A (ja) 1991-08-28 1993-03-05 Asahi Chem Ind Co Ltd 有機薄膜トランジスタ
JPH08228035A (ja) 1994-12-09 1996-09-03 At & T Corp 薄膜トランジスタ装置とその製造方法
JPH08228034A (ja) 1994-12-09 1996-09-03 At & T Corp 有機薄膜トランジスタ装置
JPH09232589A (ja) 1996-01-29 1997-09-05 Motorola Inc 有機薄膜トランジスタ
JPH1019001A (ja) 1996-07-04 1998-01-20 Nhk Spring Co Ltd メタルベローズアキュムレータ
JPH10135481A (ja) 1996-10-15 1998-05-22 Lucent Technol Inc 薄膜トランジスタからなるデバイス
JPH10125924A (ja) 1996-10-17 1998-05-15 Matsushita Electric Ind Co Ltd 有機薄膜トランジスタ及び液晶素子と有機発光素子
JPH11133205A (ja) 1997-04-21 1999-05-21 Sekisui Chem Co Ltd 反射防止膜の製造方法
JPH1176800A (ja) 1997-07-17 1999-03-23 Nippon Paint Co Ltd 貴金属又は銅の固体ゾル及び製造方法並びに塗料組成物及び樹脂成型物
JPH1180647A (ja) 1997-07-17 1999-03-26 Nippon Paint Co Ltd 貴金属又は銅のコロイド溶液及びその製造方法並びに塗料組成物及び樹脂成型物
JPH1161406A (ja) 1997-08-27 1999-03-05 Sekisui Chem Co Ltd 反射・帯電防止膜の製造方法
JPH11251601A (ja) 1997-11-24 1999-09-17 Lucent Technol Inc 半導体デバイス
JPH11319538A (ja) 1998-05-20 1999-11-24 Nippon Paint Co Ltd 貴金属又は銅のコロイドの製造方法
JP2000123634A (ja) 1998-08-10 2000-04-28 Vacuum Metallurgical Co Ltd Ｃｕ超微粒子独立分散液
JP2000124157A (ja) 1998-08-10 2000-04-28 Vacuum Metallurgical Co Ltd Ｃｕ薄膜の形成法
JP2000147209A (ja) 1998-09-09 2000-05-26 Sekisui Chem Co Ltd 反射防止フィルム及びその製造方法
JP2000121804A (ja) 1998-10-09 2000-04-28 Sekisui Chem Co Ltd 反射防止フィルム
JP2000174277A (ja) 1998-12-01 2000-06-23 Hitachi Ltd 薄膜トランジスタおよびその製造方法
JP2000185362A (ja) 1998-12-24 2000-07-04 Sekisui Chem Co Ltd 金属元素含有薄膜積層体の製造方法
JP2000239853A (ja) 1999-02-25 2000-09-05 Nippon Paint Co Ltd 金属薄膜の形成方法及び反射型液晶表示装置用反射板の製造方法
JP2001035255A (ja) 1999-07-22 2001-02-09 Vacuum Metallurgical Co Ltd 銀超微粒子独立分散液
JP2001053028A (ja) 1999-08-11 2001-02-23 Vacuum Metallurgical Co Ltd Ｃｕ薄膜の形成法
JP2001094107A (ja) 1999-09-20 2001-04-06 Hitachi Ltd 有機半導体装置及び液晶表示装置
JP2001254185A (ja) 2000-03-13 2001-09-18 Vacuum Metallurgical Co Ltd 導電性金属薄膜の形成方法およびその方法に使用する導電性金属超微粒子分散物
JP2003073382A (ja) 2001-07-09 2003-03-12 Merck Patent Gmbh チエノチオフェン誘導体
JP2004179249A (ja) 2002-11-25 2004-06-24 Mitsubishi Chemicals Corp 有機半導体材料及びそれを用いた有機電子デバイス、及び有機電子デバイスの製造方法
JP2005244236A (ja) * 2004-02-24 2005-09-08 Hewlett-Packard Development Co Lp 双安定分子スイッチ及びそれに関連する方法
JP2007059682A (ja) * 2005-08-25 2007-03-08 Konica Minolta Holdings Inc 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ
JP2007238866A (ja) * 2006-03-10 2007-09-20 Ricoh Co Ltd π共役ポリマー
JP2007311608A (ja) * 2006-05-19 2007-11-29 Konica Minolta Holdings Inc 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ

Non-Patent Citations (27)

* Cited by examiner, † Cited by third party
Title
"Kagaku Binran Kiso-hen II", 1983, MARUZEN CO., LTD.
"Kagaku Binran Kiso-hen II", 1983, MARUZEN CO., LTD., pages: 493
A. ASSADI ET AL., APPLIED PHYSICS LETTER, vol. 53, 1988, pages 195
A. DODABALAPUR ET AL., SCIENCE, vol. 268, 1995, pages 270
A.R. BROWN ET AL., SYNTHETIC METALS, vol. 68, 1994, pages 65
ADVANCED MATERIALS, vol. 13, no. 16, 2001, pages 1273
ADVANCED MATEXIALS, vol. 15, no. 6, 2003, pages 478
C.D. DIMITRAKOPOULOS ET AL., XBM J. RES & DEV., vol. 45, no. L, 2001, pages 11
F. EBISAWA ET AL., JOURNAL OF APPLIED PHYSICS, vol. 54, 1983, pages 3255
F. GARNIER ET AL., SCIENCE, vol. 265, 1994, pages 1684
FUCHIGAMI ET AL., APPLIED PHYSICS LETTER, vol. 63, 1993, pages 1372
G. GUILLAUD ET AL., CHEMICAL PHYSICS LETTER, vol. 167, 1990, pages 503
G. HOROWITZ ET AL., SYNTHETIC METALS, vol. 41-43, 1991, pages 1127
H, KOEZUKA ET AL., APPLIED PHYSICS LETTER, vol. 62, 1993, pages 1794
JANOS VERES ET AL., CHEM. MATER., vol. 16, 2004, pages 4543 - 4555
JPN. J. APPL. PHYS., vol. 42, 2003, pages 6614 - 6618
K. KUDO ET AL., SYNTHETIC METALS, vol. 102, 1999, pages 900
K. KUDO ET AL., SYNTHETIC METALS, vol. 111-112, 2000, pages 11
K. KUDO ET AL., THIN SOLID FILMS, vol. 331, 1998, pages 51
KUDO ET AL., IEEJ TRANSACTIONS, vol. 118, no. A, 1998, pages 1440
LAY-LAY CHUA ET AL., NATURE, vol. 434, 10 March 2005 (2005-03-10), pages 194
S. MIYAUCHI ET AL., SYNTHETICMETALS, vol. 41-43, 1991
See also references of EP2073290A4
T. SUMIMOTO ET AL., SYNTHETIC METALS, vol. 86, 1997, pages 2259
W. GEENS ET AL., SYNTHETIC METALS, vol. 122, 2001, pages 191
X. PENG ET AL., APPLIED PHYSICS LETTER, vol. 57, 1990, pages 2013
YOSHIDA ET AL.: "49th Spring Meeting, The Japan Society of Applied Physics", March 2002, NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2009125721A1 (ja) * 2008-04-10 2011-08-04 出光興産株式会社 有機薄膜トランジスタ用化合物及び有機薄膜トランジスタ
WO2009125721A1 (fr) * 2008-04-10 2009-10-15 出光興産株式会社 Composé chimique utilisé pour un transistor organique en couches minces et transistor organique en couches minces
JP5452476B2 (ja) * 2008-04-10 2014-03-26 出光興産株式会社 有機薄膜トランジスタ用化合物及び有機薄膜トランジスタ
JPWO2011036866A1 (ja) * 2009-09-25 2013-02-14 出光興産株式会社 有機薄膜トランジスタ
WO2011036866A1 (fr) * 2009-09-25 2011-03-31 出光興産株式会社 Transistor en film organique mince
JP5677306B2 (ja) * 2009-09-25 2015-02-25 出光興産株式会社 有機薄膜トランジスタ
JP2015109455A (ja) * 2009-09-25 2015-06-11 出光興産株式会社 有機薄膜トランジスタ
KR101800035B1 (ko) * 2009-10-24 2017-11-22 메르크 파텐트 게엠베하 액정 매질용 화합물, 및 고주파 콤포넌트에 대한 용도
JP2013508317A (ja) * 2009-10-24 2013-03-07 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶媒体のための化合物および高周波構成要素のための使用
JP2013510101A (ja) * 2009-11-04 2013-03-21 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶媒体のための化合物および高周波構成要素のためのその使用
WO2011065015A1 (fr) * 2009-11-30 2011-06-03 出光興産株式会社 Composition contenant un matériau semi-conducteur organique, et transistor à film mince organique utilisant ladite composition
JPWO2011065015A1 (ja) * 2009-11-30 2013-04-11 出光興産株式会社 有機半導体材料含有組成物及びそれを用いた有機薄膜トランジスタ
WO2011087130A1 (fr) * 2010-01-18 2011-07-21 株式会社クラレ Composé acétylénique et matériau semi-conducteur organique le comportant
JPWO2011087130A1 (ja) * 2010-01-18 2013-05-20 株式会社クラレ アセチレン化合物およびそれを含有している有機半導体材料
DE102011119293A1 (de) 2011-01-10 2012-07-12 Merck Patent Gmbh Verbindungen für ein flüssigkristallines Medium und deren Verwendung für Hochfrequenzbauteile
JP2014510710A (ja) * 2011-01-10 2014-05-01 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶媒体のための化合物および高周波コンポーネントのための前記化合物の使用
WO2012095139A1 (fr) 2011-01-10 2012-07-19 Merck Patent Gmbh Composés destinés à un milieu à l'état de cristal liquide et leur utilisation pour des composants à haute fréquence
JP2013033823A (ja) * 2011-08-01 2013-02-14 National Institute Of Advanced Industrial & Technology 有機半導体材料
JP2013035814A (ja) * 2011-08-11 2013-02-21 Ricoh Co Ltd 新規な有機半導体材料およびそれを用いた電子デバイス
JP2018513836A (ja) * 2015-02-26 2018-05-31 ソニー株式会社 フェニルエチニルナフタレン染料およびそれらの使用方法

Also Published As

Publication number Publication date
EP2073290A1 (fr) 2009-06-24
US20100012929A1 (en) 2010-01-21
TW200835009A (en) 2008-08-16
JPWO2008044695A1 (ja) 2010-02-12
CN101523631B (zh) 2010-09-22
EP2073290A4 (fr) 2011-06-15
US8217389B2 (en) 2012-07-10
KR20090077779A (ko) 2009-07-15
JP5368797B2 (ja) 2013-12-18
CN101523631A (zh) 2009-09-02

Similar Documents

Publication Publication Date Title
WO2008044695A1 (fr) Dispositif de transistor organique à couche mince et transistor organique à couche mince émetteur de lumière
JP5337490B2 (ja) 有機薄膜トランジスタ及び有機薄膜発光トランジスタ
WO2007094361A1 (fr) transistor à film mince organique et transistor électroluminescent à film mince organique
WO2008059817A1 (fr) Transistor mince film organique et transistor électrolumiscent à mince film organique
JP5299807B2 (ja) ベンゾジチオフェン誘導体並びにそれを用いた有機薄膜トランジスタ及び有機薄膜発光トランジスタ
WO2008069061A1 (fr) Transistor à couche mince organique et transistor électroluminescent à couche mince organique
KR20110057133A (ko) 유기 박막 트랜지스터용 화합물 및 그것을 이용한 유기 박막 트랜지스터
KR20110063747A (ko) 유기 박막 트랜지스터용 화합물 및 그것을 이용한 유기 박막 트랜지스터
WO2010024180A1 (fr) Composé pour transistor à couches minces organiques et transistor à couches minces organiques utilisant le composé
TWI423341B (zh) Organic thin film transistor and organic thin film emitting transistor
JP5452476B2 (ja) 有機薄膜トランジスタ用化合物及び有機薄膜トランジスタ
JP2015109455A (ja) 有機薄膜トランジスタ
JP5308164B2 (ja) 有機薄膜トランジスタ及び有機薄膜発光トランジスタ
JP5528330B2 (ja) 有機薄膜トランジスタ用化合物及びそれを用いた有機薄膜トランジスタ
JP5452475B2 (ja) 有機薄膜トランジスタ用化合物及びそれを用いた有機薄膜トランジスタ
JP5329404B2 (ja) 有機薄膜トランジスタ及び有機薄膜発光トランジスタ
JP2008147587A (ja) 有機薄膜トランジスタ及び有機薄膜発光トランジスタ
JP5308162B2 (ja) 有機薄膜トランジスタ及び有機薄膜発光トランジスタ

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200780037982.X

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07829467

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2008538733

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 2007829467

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 12445146

Country of ref document: US

Ref document number: 1020097007448

Country of ref document: KR

NENP Non-entry into the national phase

Ref country code: DE